#40 Bob Dylan- The Freewheelin’ Bob Dylan
- agalvin19
- Aug 13
- 5 min read
Updated: Aug 19
Better late than never: Bob Dylan gets a hit, and it only took two years…
(CBS)

Released: 27th May 1963
Producer: John Hammond, Tom Wilson
Topped the chart:
11th April 1965 (for 1 week)
16th May 1965 (for 1 week)
2 weeks total
We’ve previously explored the difficulty of reviewing The Beatles in the 21st century at the foot of so many column inches. Bob Dylan is the only artist who presents even more of a challenge. Here is a man whose every footstep from 1960 to 1980 has been written about, usually at least twice. His very existence is what allowed this nascent “rock” music to be taken seriously—without Dylan there would be no navel-gazing self-important rock bibles like Rolling Stone or MOJO magazine to analyse music until it loses all meaning. If you’ve ever read this blog thinking, “God this guy is taking pop music a bit seriously…” well, now you know who to blame.
There are plenty of other people steeped in Dylan lore who are better placed to explore the link between Dylan’s brand of pop and traditional folk songs, and his second album, The Freewheelin’ Bob Dylan has been dissected more often than a turkey farm at Christmas. Instead of covering old Boxing Day leftovers, let’s explore why Freewheelin’ became a big British hit two years after its initial release, and why it remains Dylan’s most enduring album in the public consciousness.
It all comes down to a confluence of the spheres: a combination of the right people, the right talk, the right songs and the right tour.
Four of those people were, of course, The Beatles. Each interview the Fab Four conducted was poured over by thousands of people, so them putting their blessing on another musical act would get their records moving. It’s like the Nigella Lawson factor, where Bob Dylan was goose fat. It was Paul McCartney who was the first to discover Dylan after “cadging” a pre-release copy of Freewheelin’ from his brother Mike. Apparently nonplussed at first (“This guy can’t sing,” as Mike quotes his brother), he was eventually won round and shared the record with his bandmates.
Lennon was particularly taken with Dylan and was the first to explicitly take on his influence: his lyrics became more poetic and thoughtful, his voice more nasal and his use of acoustic rhythm guitar gave the game away and, as a result, Beatles fans were somewhat prepared for the new sound Dylan was ushering in.
As the LP came of age, a half decent cover image didn’t exactly hurt—Bob and then girlfriend Suze Rotolo wrapped up against the chilly New York autumn and they slush through the sleet at their feet very quickly became iconic, representing a statement of intent from a class of increasingly socially-conscious students showing off how they understood the issues Dylan was protesting maaaaaan—we’ll return to this.
Of course, many of them were gearing up to attend Dylan’s legendary debut English tour in April and May 1965, his biggest and most discussed tour of the country to date- it was the first time one of Bob's foreign sojourns had a buzz about it. In the studio in 1965, Dylan was making music entirely different to the contents of Freewheelin', but performing live, it was still just he and an acoustic guitar, so the sound of this record would still have felt very present.
And finally, perhaps most importantly, there’s the sound of the thing. No one heard Dylan’s self-titled album, but for those few who did, it’s a world away from what we have here: punky, rough and hard-edged. It’s pleasantly underrated, but here the addition of Tom Wilson as co-producer (alongside a returning John Hammond) makes a world of difference. The ambience of these songs is warm and inviting, intimate and close. It might be one of the first mainstream albums to feel like the artist is in the room himself: The likes of Girl from the North Country (particularly affecting finger-picking guitar style was a big help), Oxford Town and Corrina, Corrina feel like they’re being sung to us as individuals, a feature that makes it that little bit easier to get over his acquired taste of a voice.
Nothing more needs to be said about Blowin’ In the Wind, and the protest songs are the ones people tend to remember. It helps that the blatant, raging Masters of War and the more poetically opaque A Hard Rain’s a-Gonna Fall and Oxford Town are among the most memorable performances on the album (though Dylon would later dismiss his protest songs: in 2001, Dylan said that he just “picked [the mood] up” from the air of the time, and even when recording a demo of Blowin’, Dylan can be heard saying “this here ain’t a protest song, or anything like that, ‘cause I don’t write protest songs.” Protest would remain in the air around Dylan for the following record, 1964’s The Times They Are a-Changing but, by the time Freewheelin’ hit number one in 1965, Dylan had already moved on
Crucially, there’s a lot more to Freewheelin’ than just politics which perhaps explains why it appealed to the wider British public so strongly, and a lot of what Dylan would go on to achieve in the rest of the decade can be found here.
Not only that, but so much of what Dylan would achieve in the next decade can be found on Freewheelin’. The abstract poetry that got critics so excited on his 1965 albums, Bringing It All Back Home and Highway 61 Revisted is starting to bleed through on Bob Dylan’s Dream and I Shall Be Free (closing with the couplet, “I make love to Elizabeth Taylor/Catch hell from Richard Burton"), Talkin’ World War III Blues and Down the Highway capture the feel of his more expansive, rambling album future album closers like Desolation Row and Sad Eyed Lady of the Lowlands. Dylan would usually approach affairs of the heart obliquely, but Girl From the North Country is nakedly romantic in the style of If Not For You and Make You Feel My Love, while the darker edge of Don’t Think Twice It’s Alright would be perfected on 1975’s Blood on the Tracks.
There's even early evidence of his slightly forced higher-pitched country voice from 1969's Nashville Skyline on Corrina, Corrina. It's all here.
Of course, Freewheelin’ doesn’t the squalling electric guitars that saw Dylan really revolutionise, but they weren’t very far away. Pete Seeger might have been upset to see Dylan move away from the folk interpolations here, but it was clear that for Dylan in 1965, the times they were a-changing…
Score: 9/10
Tracklisting:
SIDE A
1. Blowin’ in the Wind
2. Girl from the North Country
3. Masters of War
4. Down the Highway
5. Bob Dylan’s Blues
6. A Hard Rain’s a-Gonna Fall
SIDE B
7. Don’t Think Twice It’s Alright
8. Bob Dylan’s Dream
9. Oxford Town
10. Talkin’ World War III Blues
11. Corrina, Corrina
12. Honey, Just Allow Me One More Chance
13. I Shall Be Free
The Beatles and Dylan's relationships are fascinating. McCartney and especially Lennon heard Dylan which made them want to move away from fluffy pop tracks to more meaningful song writing. Dylan, on the other hand, heard the Beatles which made him want to write better tunes to his poetry, which he at various times did. As you stated, Lennon's affection for Dylan can be mostly heard in his songwriting. It was George Harrison who became a close friend of Dylan and who was most willing to openly fawn over his artistry - rightly so in my opinion!
Great article.